Nights Like This
by MidnightEpiphanies
Summary: Elena Gilbert is a witty escort simply putting herself through college. Damon Salvatore is a savvy businessman determined to get over his ex-fiancé. When two chance meetings occur, the two soon realize that maybe there isn't such a thing as coincidence after all. AH, DE.


Don't hate me! (shields self) I know how absent I have been on here, and I'm so sorry for that. I'm in the home stretch of my senior year of HS and have been chomping at the bit with homework. During my free time, I'm focused on my book, which is based off of my original ff, Shelter, as some of you may know. I have been haunted by this idea for months and have finally taken some time off of my book to work on this. I know that I do NOT need another FF, but as I'm in the midst of wrapping TOSOM and It's Complicated up, I felt I needed a new fresh start. I do plan to finish those two stories, but unfortunately, I cannot give a date as to when those will be updated. I can however hopefully satisfy those of you who read either or both of those stories that I know how they will end; I just need to sit down and get into the mind-set of those stories.

So, without further or due, I present to you, a new fanfic which I hope you will all like. An in-depth synopsis is below.

Thanks all for your understanding and hope that you like this!

xoxo

* * *

**~*ONE*~**

One of the best, and worst, things about my job is the fact that no two clients are ever the same.

And I'll be damned if I experience another client like this anytime soon.

As I finish snapping my two karat diamond earrings into place, I crane my neck back to see my latest conquest slumbering softly against in of the most comfortable beds I've ever woken up in. The events of last night are no more than a blur thanks to the four or so Martinis I consumed at one of the better-organized functions I've attended. Then again, when you're on the arms of a sixty-something year-old man, odds are that it's for something Clinton might even be attending. These are the guys that know business like I know my way around the male body. And that's something I mastered when other girls begin the puberty phase. A slight buzz steals my attention, and I twist around to see my phone light illuminated. Leaning forward, I clutch it in my hands as I read the words displayed on the screen:

_REMINDER: Marriott Hotel, room 306 in one hour and thirty minutes_

Glancing up at the clock in the upper right corner of my phone, I'm shocked to see it's not even ten-thirty yet. It's a rare occasion when a client wants to meet before lunch, unless of course I'm traveling with them. Sighing as my day has officially begun, I stand up from the edge of the bed and move to gather my clothes, which are scattered across the floor of Mr. Jeffery Lockwood's fine Richmond apartment. My Pradas are hiding in the corner underneath his blazer, and as I bend down to retrieve them, I catch an overwhelming whiff of what I'm ninety-nine percent certain to be some Calvin Klein woman-seducing tool. I roll my eyes. The only time that this kind of thing works is when you see the woman climbing over the table for you in some promo on television. Otherwise, it's all bull.

As I glance back at myself through the mirror hung against the wall, I quickly primp my messy chocolate curls with my travel-size brush. Thanks to Mr. Lockwood, he did a number on me yesterday, and even my hair paid the price for it. God, that man sure doesn't act his age, if you know what I mean. Once I am satisfied with my appearance, I stow my brush back in my oversized Louis Vuitton, leave my room key where my check rests, and make my way toward the door.

Once I hear the door close behind me, I pull out my Chanel sunglasses and prop them over my eyes as I saunter down the hall. I pass an elderly woman who gives me a look similar to how the Pope would eye a prostitute. I don't even flinch; I've gotten used to the judgement over the last few years in this business. It's just a brush of the shoulder and I go on with my day. As the brilliant Miley Cyrus says, only God can judge us.

And as far as I know, that woman was not God.

So with as much pride as I can gather, I strut down the staircase, ready for another day and ready for another grand to land in my pocket.

* * *

"He was _how_ old?" Caroline cries as she nearly chokes up her Tiramisu. Her oceanic blue orbs regard me as if I told her I decided to become a man.

That'll be the day.

"Old enough to file for retirement, I'm sure," I shrug as I take a sip of my caramel latte, suddenly regretting my decision to tell Caroline about my client from last night. Hell, scratch that. I regret telling her about my job in general. But there are only so many things you can hide from your roommate. Especially when that roommate is known for knowing everything. In fact, I'm pretty certain that she knows who will be the next president.

"Oh, my god," Caroline sighs as she reclines in her seat. "You don't have any limits, do you?"

Without hesitance, I shake my head. "The older, the richer." I arch a playful eyebrow at her, grinning like a schoolgirl.

"Ew," she makes a face as her eyes screw shut. "I think you've just ruined my appetite, thank you very much."

"Oh, don't fret," I pout as I pull out my wallet. "How much was that?" I nod toward her drink, and she blinks. I'm sure she didn't expect me to pull that one out of the hat.

"It's fine," she says dismissively.

Too dismissively...

"You can pay me back by going out to dinner with Enzo and I tomorrow night."

And there it is!

"What do you mean?" I frown. "I thought Bonnie was going with you guys after her Music Theory class."

Bonnie Bennett, a.k.a. our other roommate at Georgia State, is known for enduring Caroline when no one else can. Me included. So why she dropped out on the Carenzo date night is a mystery to me.

"She was going to, but her Grams is driving up to spend the day with her," She mutters petulantly, and Caroline's ever-familiar selfishness is shining through.

"Well, I would go, but I-"

"Oh, bullshit." She snaps. "You don't have any plans tomorrow night. Other thank studying for your English Lit Exam, which you're going to ace, of course."

Just when I'm about to ask her how the hell she knows what my plans are or aren't tomorrow, I remember that my planner is spread out on the kitchen table.

Damn.

"And you owe me," She smiles, and it's one of those smiles– the ones that are too damn certain for their own good.

"Oh, thank you, thank you, thank you!" She blurts out as she dances in her seat. Caroline Forbes, ladies and gentlemen.

"Don't mention it," I smirk as I dig around my purse for my phone. It's quarter to eleven, which means that I have about fifteen minutes until I'm meant to be undressed and waiting in bed for client numero dos.

"Time to go rock another lonely man's world?" Caroline saunters playfully, and I roll my eyes at her.

"Bite me," I scoff mockingly, standing up from my seat. Caroline mirrors my actions.

"Oh, honey, it looks like he's already got that covered." Her voice drips with audacity, and for the first time in a long time, I'm rendered speechless.

"You're a piece of work, Forbes," I shake my head as we exit the café, not quite sure how to respond to that.

"Oh, I'm definitely hard work, if you know what I mean," Caroline winks at me, and I can't resist the fit of laughter that escapes my lips.

"Save that for Enzo," I holler as we part ways.

"Oh, believe me, I will," She grins as she opens the door to her Bentley.

And with that, I climb in my Cherry flavored Mercedes convertible and blast the radio as I pull out into traffic.

* * *

I'm in the elevator on my way up to the third floor of the Marriott Hotel. This is when I get any sort of nerves. I don't know what this guy looks like. He could be a Tatum or he could be a Cage. Who knows? It doesn't even matter what he looks like. I know he sounds sexy. His voice over the phone sounded like warm chocolate was oozing down through the line. All I hope is that he's at least halfway as attractive as his voice made him sound. I sigh, knowing that the odds are unlikely. Regardless, I have one job to do:

Pleasure him to the best of my ability.

As I adjust my skin-tight, ruby dress over my well-defined breasts, I'm sure that the dress alone will pleasure him enough.

The ping of the elevator awakens me from my thoughts and I step out into the vacant hall, my Chanel suitcase lugging behind in tow. I take out my phone and pull up the appointment reminder to check the room number. 306. I glance up to see the directory sign that tells me that rooms 301-320 are left.

As I approach the suite, I notice the key peeking up at me through the crack. I bend down and pick it up, slide it in the lock, and with a click as my signal, I enter.

The room is a decently sized suite. Olive green carpet laced with a light yellow flower pattern spread out across the floor. Creamy white walls surround me. To the right of me is the entrance to the bathroom, and as I walk further in, I see the king-sized bed in the center of the room. I instinctively run my hands agains the silky fabric, anticipating it's feel around my body.

My phone buzzes in my jacket pocket, and I pull it out to see the 15 minute warning. I hop off of the bed and drag my suitcase into the bathroom with me. I pull out my most popular lingerie, a lace black corset, paired with black underwear and fishnet stockings. I normally go bare, but because this client didn't request anything, I decide to take my chances with the lingerie. It's not like I've had negative reviews of it. Once I'm dressed, I run my fingers through my hair in attempt to make it look more voluptuous and sexy. I quickly apply my Very Cherry lipstick on, and finalize the look with a quick dash of Chanel No. 5. Deciding I'm satisfied with my appearance, I make my way to the bed and spread myself out on it. As the door knob jiggles, I finalize my position. When the sound of footsteps echoes against the floor, my nerves return with the anticipation.

Please be younger than 40, please be younger than 40.

As I search around the corner, I see only back; a very sexy back, I must add.

And when he turns around, I don't know who is more shocked.

Holy fuck, he's sexy.

Tousled, ebony hair frames the most attractive face I've seen. And I've seen a lot of faces. His features are defined so well that Michelangelo himself would be proud. But those eyes...

Those baby blue eyes that regard me hungrily stir my insides in a way that hasn't happened before. If only I could fuck those eyes.

Realizing that its been too long without saying anything, I decide to speak up.

"Hello, handsome," I call flirtatiously, waving him over with a finger. "I've been waiting for you,"

His eyes immediately flash with desire, and I just want to jump him right now.

"Have you?" He smirks, and I sense a bit of cockiness.

"Yes," I nod, twirling my legs. "Why don't you get that fine ass over here before I come over there and drag you over?"

If I thought his eyes looked hungry earlier, they look absolutely starving now.

"Well, what if I want you to come over here?" He challenges, and I bite my lip in excitement.

"Then I would have to say that I live to pleasure," I respond as I climb off of the bed and saunter my way over to him. He eyes me intently, and I can't get a clear reading from him.

As I approach him, I reach out my hand and grab his tie in my hands, yanking it toward me. His hands land with ease in my waist, and I shake my head as I pout.

"You read my mind" I whisper, pulling him closer to me until my lips are at his ear. "I want to feel you," I breathe as I reach for his belt with my free hand. Within seconds, I have his belt unbuckled and am pulling him closer to me by the waist. Immediately, I slide my hand over his pants, skimming his arousal, and I grin with satisfaction as I hear him attempt and fail to stifle a moan.

"You like that, huh?" I whisper, splaying my hand over his growing erection. I wait for him to respond, but am instead blindsided as he pushes me onto the bed.

"Enough," he growls as he slides out of his pants and into his underwear. His shirt comes off next, and within seconds, he's hovering over me, and his lips are on mine.

Holy fuck, his lips are addicting. I wrap my arms around his back, but he shakes his head. "You had your fun," he says in between kisses. "Now it's my turn. I want to get you bare for me,"

With ease, he moves his hand down to the hemline of my corset and begins to pull it up. His lips abandon mine as the lower onto my exposed stomach. The soft and electric feeling of them on my flesh startle me, and I let out a sharp moan.

"Hush," He says as his lips climb up my torso. When I feel them at the base of my breasts, I arch my back in response. God, I can't remember the last time I was this turned on.

"Ah!" I cry as his lips close around my left nipple. His hands slowly trace up my arms and pin them to the mattress.

"Lift your arms up," he says, and I comply with grace as he pulls my corset over my head.

"Good girl," he grins sexily, and I shake my head.

"Elena," I correct.

"Pleasure to meet you, Elena," he chuckles, "I'm Damon."

"Well, Damon," I breathe, "I believe-" I thrust my hips into his, feeling his erection at my center. "-the pleasure is mine."

"You're a feisty one, aren't you?" He smiles. I nod, returning his grin.

"I like that," he confesses.

"Good," I respond hazily, feeling drunk off of his voice alone.

"Now," he begins, reaching down toward my waistline. "Let's get you out of these very sexy panties,"

With that, I explode with laughter.

"Not the response I expected," he says nonchalantly.

"I'm sorry," I shake my head, my laughter dying down. "I just can't believe you said panties,"

"What are you, twelve?" He grins, and I roll my eyes.

"Some would say so." I admit.

"Oh, is that so?"

"Yes, so."

"Well, enough chit-chat," he chastises, and his lips are over mine in a second, His hand slithers down into my underwear, and I fidget against the bed in response. When he slides one finger in, I cry out as he brushes his lips over my neck.

"You're so beautiful," He breathes against my flesh, and I can't resist as my body surrenders, exploding all around me.

"Argh!" I scream, and as I climb down from the high, I feel a momentary vacancy as he moves to pull my stockings and underwear off. In what seems like forever, he's hovering over me once again. I feel his arousal at my center, and when he slams into me, I cry out all over.

"Fuck," he grunts as he withdraws, then enters again. "You're so tight,"

"Thank you," I giggle as I grip his shoulders in attempt to ease his access.

"You're a smart-ass," he assesses as he enters me again, the feeling absolutely thrilling. "It's sexy,"

"You too," I blurt out, too high off of him to give a damn what I'm saying.

"Yes, I am," he nods. I'm about to respond, but my orgasm face-palms me and I cry out again.

"Fuck," he breathes as he enters me one last time. I barely catch my breath when he falls onto me.

"You sure know how to drive a man crazy," Damon sighs as he rolls over onto the other side of me. I turn around and prop myself up on my elbo.

"Well, when you do what I do, it's a requirement," I remind him as I raise an eyebrow at him playfully.

"How long have you..done this?" He asks, all humor aside.

I rest my arm as I lay on my backside. "Since I was 18."

"Why so early?"

Damn.

Way to be a mood killer.

"It's a long story." I dismiss.

"I bet."

Silence...

"I should go," Damon says after a while. I turn over to see him resting on the side of the bed.

"Oh?"

"I have to get ready for a meeting later," he says softly, and I wonder if he's leaving because of me, or because of him.

"Alright," I nod, sitting up.

"How much do I owe you?"

Huh?

I glance up to see him standing with his checkbook in hand.

Oh.

"Seven-fifty." I say. "And it's Elena Gilbert."

Nodding, Damon scribbles the info onto the check, tears it out artfully, and then hands it over to me.

"Thank you," I say as I take it from him.

"No, Elena," He shakes his head, a gleam of excitement in his eyes. "Thank _you,"_

Cocky's back!

"Have a nice day," I say, realizing too late that this sounds absurd.

"You too," he smirks as he exits the room.

Once the door closes, I look down at the check.

Damon Salvatore

Pay to the Order of: Elena Gilbert

For: Personal Assistant

I immediately let out a fit of laughter once I see the 'Personal Assistant'.

As My eyes skim the rest of the check my eyes nearly pop out of my head when I see how much he paid me.

Amount:$1,200

This was a mistake.

I brush the sheets off of me as I fetch a nearby robe. I whisk the door open and turn both left and right, but when I see only a young woman on her cell phone, I realize that I'm too late.

Walking back into the room, I can't help but begin to wonder that the overpayment wasn't accidental.

* * *

Well, I hope you all liked it! It's about 5 am here, so toward the end the writing got a bit sloppy :/

**AN:**PLEASE FAVE/FOLLOW. Oh, and PLEASE **_REVIEW :) _**Every review is a virtual hug to me (not to sound creeperish D:)!

**PS:** Check out my other TVD/DE fanfic stories! I'd appreciate it :)

**PPS: **_Follow_ me on Twitter at EverbloomMist13!

* * *

(THEME SONG) _**Stay**_Rihanna

Soundtrack that inspired/mentioned in this chapter:

**_From the Wreckage Build A Home ~_** The Wind and the Wave (Elena and Caroline talk at Starbucks)

_**Fleur Blanche~**_ Orsten (Bedroom scene)


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